Anthelmintic constituents of ferns

Abstract

Extracts, oils and some individual phloroglucinol compounds prepared from the fern Dryopteris dilatata and Dryopteris filix-mar were tested for taeniacidal activity against the dwarf tapeworm Hymenolepis nana. In D. dilatata activity is concentrated in the phloroglucinol compounds (mainly aspidin, phloropyrone and aspidinol) of which aspidin is the most potent. In D. filix-mas the mixed phloroglucinol compounds (mainly flavaspidic acid and aspidinol) are active, but no more so than the total ether extract. Flavaspidic acid seems to be the most active phloroglucinol constituent of the fern. Desaspidin which occurs in a third fern, Dryopteris austriaca, is more potent than either aspidin or flavaspidic acid. A method of detecting phloroglucinol compounds by thin-layer chromatography is described.

Gastrothylax crumenifer: ultrastructure and histopathology study of in vitro trematodicidal effect of Microlepia speluncae (L.) Moore

“…The medicinal uses of Pteridophytes have been viably reported (Benjamin & Manickam 2007;Benniamin 2011). The anti-trematodal property of flowering plants has been reported worldwide (Hossain et al 2012;Alvarez-Mercado et al 2015); Blakemore et al (1964) and Amritpal Singh (2011) reported on the anthelmintic property of ferns. Kalpana Devi et al (2016) reported on the anti-trematodal property of Blechnum orientale against Gastrothylax crumenifer.…”

The Effect of Male Fern Extract on Biliary Secretion

“…Male fern extract is an ether extract of Dryopterisfelix-mas rhizomes containing a number of substances including filicin, flavaspidic acid and aspidinol (Blakemore, Bowden, Broadbent & Drysdale, 1964). Runeberg (1962) showed that flavaspidic acid and aspidinol uncoupled oxidative phosphorylation.…”

Some Simple Anthelmintics

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The substances mainly responsible for the anthelmintic activity of the rhizomes of male fern (Dryopterisfilix-mas) and related plants were shown by Boehm early in the century to be complex phloroglucinol compounds, of which examples are flavaspidic acid and aspidin.More recently the structures of related active compounds occurring in ferns have been elucidated by Penttila & Sundman (1963 and earlier papers). Aspidin and desaspidin have been shown to be among the most active in the series (Blakemore, Bowden, Broadbent & Drysdale, 1964).Although these compounds are effective against certain helminthic infections, they are not readily obtained in quantity from natural sources and their synthesis is not easy.The object of the work was to find simpler phloroglucinol or related compounds with an anthelmintic action and which could be readily synthesized. During the preparation of substances related to desaspidin it was found that the simple compound diacetylphloroglucinol had appreciable activity in vitro against Hymenolepis nana.

HO-OH CHOCO OOCH3 OH D iacetyl ph lorogl uci nol A series of related compounds, with structures I to VI, has been prepared in order to find the structural requirements for anthelmintic activity.

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“…More recently the structures of related active compounds occurring in ferns have been elucidated by Penttila & Sundman (1963 and earlier papers). Aspidin and desaspidin have been shown to be among the most active in the series (Blakemore, Bowden, Broadbent & Drysdale, 1964).…”

“…More recently the structures of related active compounds occurring in ferns have been elucidated by Penttila & Sundman (1963 and earlier papers). Aspidin and desaspidin have been shown to be among the most active in the series (Blakemore, Bowden, Broadbent & Drysdale, 1964 Although these compounds are effective against certain helminthic infections, they are not readily obtained in quantity from natural sources and their synthesis is not easy.…”